Summary: Imogen Moreno would be his biggest challenge yet.

Disclaimer: Don't own Degrassi. 'Nuff said.

Author's Note: This was inspired by the fic "Life From a New Perspective" by MonsterMind. UPDATE! FOR THE LOVE OF GOD, UPDATE!

Also, I'd like to thank Asya (misfitsandco on Tumblr) for helping me brainstorm!

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Challenge
By: Lady Azura

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It was a crisp November morning; the air was colder, and winter was just around the corner. Christmas was only weeks away and every other house on the street was decked out for the holidays.

As students filed into the school in their jackets and hats, crowding the decorated halls and joining their friends, Jake Martin found himself alone. He sat in Degrassi's zen garden, right next to a large memorial, staring out the glass window at his now ex-girlfriend.

Nearly a month had passed since Helen and his dad had found out about him and Clare.

Again.

Needless to say, their parents had been less than thrilled to walk in on Clare straddling him in nothing but her bra and jeans. There had been a lot of yelling before Clare grabbed her shirt and left in tears. She didn't return until much later that night, and when she did she was like an entirely new person. To him, anyway. It was as if she'd had some sort of epiphany. No longer hysterical, she took him aside and broke up with him. Just like that. She wasn't cruel about it, but rather matter-of-fact instead, saying that they had been foolish to think that they would last forever.

"All I've done is hurt people… I don't even know who I am anymore…"

Her words echoed in his mind over and over again, and he found it weird how she said she had hurt people — like he hadn't played a role in it at all.

While relieved (because — and he would never admit this — the thought of "forever" scared the crap out of him) he couldn't help but feel… heartbroken. Clare was his first real relationship, even if it had been a bit unconventional and weird trying to play two roles — her brother in front of their parents and her boyfriend the rest of the time. It didn't help when he saw her hanging out with Eli, and he had a feeling that she'd run into Eli the night they broke up. Eli seemed to be the only person who really ever got her and vice-versa. Even after everything that had happened the year before, they still managed to salvage a strong friendship. And Jake knew that they were only friends, but he also saw the way that Clare looked at Eli — and that she had never looked at him quite like that.

But it still hurt.

Just a little bit.

"It's over." A voice chimed into his thoughts, and when Jake glanced over, he found a bespectacled girl sitting across from him.

He recognized her instantly as one of Eli's friends. She was in his English class too, but he couldn't place a name. Isabelle? Ileana? Isadora?

"Imogen Moreno," the girl announced, as if reading his mind.

"What?" He asked dumbly.

Imogen tightened one of her messy pigtails before looking back at him.

"Whatever you and Clare Edwards had is over, and there's no point in brooding about it." She said simply.

Jake furrowed his brow. "Excuse me?"

"Are you really that dumb?" Imogen asked, before letting out an annoyed sigh. "Jake Martin, you might be cute, but you're about as savvy as a doorknob."

"You're really the last person who should be judging anyone…" Jake countered slowly, eyeing the cat ears perched on her head. "Besides, you don't know anything about me."

"I know enough." Imogen stated, adjusting her glasses. "I'll have you know I'm very observant."

"You're crazy," Jake muttered, rolling his eyes.

"And you're boring." Imogen retorted.

"What?"

"Oh, don't act so surprised." Imogen said, reaching into her bag and pulling out a sketchbook. "It was only a matter of time before Clare lost interest in you."

"You don't know anything!"

"I know a lot more than you think."

"Oh, yeah?" Jake challenged.

Imogen nodded curtly.

Jake scoffed. "Right. Whatever. If you were so smart, you'd know that we broke up because our parents caught us - not because Clare lost interest."

"Your parents walking in on you merely sped up the process. But sooner or later, Clare would've left. Like I said… you're boring." Imogen stated as she doodled in her sketchbook. "Although… so is she. I could never quite understand what everyone sees in someone so… plain. I mean, really, you'd think you guys were a perfect match, but I guess you were so boring that she had no choice but to leave for someone a little more… exciting."

"What? What are you talking about?" Jake sputtered, more than a little offended. "I'm not boring! Me and Clare had lots of fun!"

"Yes, I'm sure sneaking around with one's step-brother does add a certain element of fun… but how long did you think that would last?" Imogen asked.

"I… I don't know…" Jake's mind was jumbled.

"Face it. By the time you two finally split, the 'magic' was gone." Imogen replied. "Like I said… you're boring. You avoid drama like the plague and you don't seem to have any interests except for sticking your tongue down your sister's throat. Do you see what I'm getting at?"

"I've heard I'm a pretty good kisser." Jake said smugly.

Imogen rolled her eyes.

"Boring and cocky." She deadpanned.

Jake frowned.

"So if I walked up to you in the middle of the hall and asked you out, you wouldn't be the slightest bit interested?"

Imogen let out a laugh.

"In your dreams, Jake Martin. You're cute, I'll give you that, but I like a little excitement in my life and I'm afraid you're the complete opposite of that." She said with a smirk.

"I can be exciting." Jake told her.

"Dating your step-sister isn't new or exciting. I've seen Clueless, you know."

The first bell sounded, signalling the start of class. As students scurried around and rushed to their classes, Imogen put away her sketchbook and slowly stood up. Jake watched her, his gaze instinctively wandering, and soon he found himself staring at her bare legs. It blew his mind how girls could wear skirts in the winter, but he certainly wasn't complaining.

"So long, Jake Martin. I'll see you around." Imogen said as she shouldered her bag and made her way out into the hall.

Jake sat still for a few minutes before quickly scrambling to get up. After grabbing his own bag, he chased after her. Once he managed to catch up with her, he caught her by the wrist and pulled her into an abandoned classroom.

"What are you doing?" Imogen demanded, narrowing her eyes dangerously.

Without a word, Jake leaned down and pressed his lips against hers.

The kiss was short, only lasting a few seconds. When Jake drew back, Imogen was blinking in confusion, as if trying to register what had just happened. Once the shock wore off, however, she smirked up at him.

"Sorry, but you're gonna have to work a lot harder than that." She said, before brushing past him and walking out the door.

As he watched her leave, a small grin tugged at his lips.

Imogen Moreno would be his biggest challenge yet.

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FIN

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So… that's that.

I really didn't know how else to end it, but I hope you guys enjoyed nonetheless.

Please REVIEW and tell me what you think!